Dicationic Electrophiles from Olefinic Amines in Superacid

Dicationic Electrophiles from Olefinic Amines in Superacid

This paper describes the superacid-catalyzed chemistry of olefinic amines and related compounds. A variety of olefinic amines are found to react with benzene in CF3SO3H (triflic acid) to give addition products in good yields (75−99%), including the pharmaceutical agents fenpiprane and prozapine. A g...

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Veröffentlicht in:Journal of organic chemistry 2003-06, Vol.68 (13), p.5119-5122
Hauptverfasser: Zhang, Yun, McElrea, Aaron, Sanchez, Gregorio V, Do, Dat, Gomez, Alma, Aguirre, Sharon L, Rendy, Klumpp, Douglas A
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Sprache:eng
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Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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container_end_page 5122
container_issue 13
container_start_page 5119
container_title Journal of organic chemistry
container_volume 68
creator Zhang, Yun
McElrea, Aaron
Sanchez, Gregorio V
Do, Dat
Gomez, Alma
Aguirre, Sharon L
Rendy
Klumpp, Douglas A
description This paper describes the superacid-catalyzed chemistry of olefinic amines and related compounds. A variety of olefinic amines are found to react with benzene in CF3SO3H (triflic acid) to give addition products in good yields (75−99%), including the pharmaceutical agents fenpiprane and prozapine. A general mechanism is proposed that invokes the formation of reactive, dicationic electrophiles and the direct observation of a diprotonated species is reported from low-temperature NMR experiments. This chemistry is also used to conveniently prepare functionalized polystyrene beads having pendant amine groups.
doi_str_mv 10.1021/jo030024z
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subjects Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
title Dicationic Electrophiles from Olefinic Amines in Superacid
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